Benzyl chloroformate → 2-[(benzyloxy)carbonyl]-1H,2H,3H,4H,9H-pyrido[3,4-b]indole-1-carboxylic acid

HRID 742870ノート

反応式

HRID 742870 の反応式
[CH:1]1([C:14]([OH:16])=[O:15])[C:6]2[NH:7][C:8]3[C:13]([C:5]=2[CH2:4][CH2:3][NH:2]1)=[CH:12][CH:11]=[CH:10][CH:9]=3.Cl[C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19]>[OH-].[Na+].O.O1CCOCC1>[CH2:21]([O:20][C:18]([N:2]1[CH2:3][CH2:4][C:5]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][C:6]=2[CH:1]1[C:14]([OH:16])=[O:15])=[O:19])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

参加物

6

反応物 2

HCID 10387Benzyl chloroformateHCID 1458792,3,4,9-Tetrahydro-1H-pyrido(3,4-b)indole-1-carboxylic acid

生成物 1

HCID 190319922-[(benzyloxy)carbonyl]-1H,2H,3H,4H,9H-pyrido[3,4-b]indole-1-carboxylic acid

試薬・触媒・溶媒 3

HCID 962Water溶媒2 回HCID 14798Sodium Hydroxide溶媒2 回HCID 312751,4-Dioxane溶媒2 回

実験手順

To a solution, cooled in ice, of 3.0 g of 1,2,3,4-tetrahydropyrido[3,4-b]indole-1-carboxylic acid in 7 ml of 2M sodium hydroxide solution, 17 ml of water and 17 ml of dioxan were added in alternating portions 12.5 ml of 2M sodium hydroxide solution and a solution of 3.6 ml of benzyl chloroformate in 9 ml of dioxan. After completion of the additions the mixture was stirred at room temperature overnight and the dioxan was then removed by evaporation under reduced pressure. The solution obtained was diluted with water, washed twice with diethyl ether, acidified with 25 ml of 1M sulphuric acid and extracted three times with ethyl acetate. The organic extracts were combined, washed twice with water, dried over anhydrous magnesium sulphate and evaporated to give 4.54 g of 2-benzyloxycarbonyl-1,2,3,4-tetrahydropyrido[3,4-b]indole-1-carboxylic acid, MS: m/e 351 [M+H]+, which was used without purification.

後処理

  1. additionwere added
  2. customthe dioxan was then removed by evaporation under reduced pressure
  3. customThe solution obtained
  4. washwashed twice with diethyl ether
  5. extractionextracted three times with ethyl acetate
  6. washwashed twice with water
  7. dry with materialdried over anhydrous magnesium sulphate
  8. customevaporated

出典と根拠

ORDレコード
ord-96dac4fd734d4150961e439a7c4db157
出典データセット
uspto-grants-1996_09
特許番号
US05554756

反応ノート

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